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Siena in Tuscany

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Hidden highlights of Tuscany

By Italy specialist Kimberly

Tuscany is a region of green rolling hills, wineries with cypress trees lining the driveway, the terracotta rooftops of Siena, and Florence’s Uffizi and Accademia galleries.

As I’ve come to know it better, I’ve found ways to experience Tuscany beyond the obvious sights. Not all art in Florence is found in grand galleries. You can get a feel of Tuscan architecture and ambiance in smaller, less frequented towns such as Lucca. You can get to know Tuscany’s countryside and its food heritage by exploring the arts of honey making and truffle hunting under the guidance of experts.

What to do in Florence

View across Florence

View across Florence

Once an independent city state, Tuscany’s capital still retains its medieval street plan of sinuous, narrow alleys. Palazzos (palaces), churches and art museums house masterpieces from Florence’s Renaissance zenith. Across the River Arno and at the fringes of the central area are livelier, modern residential districts, many of which have been revived and gentrified.

If you’re planning on visiting the Uffizi or Accademia, the city’s biggest galleries, go with a guide. They can help you negotiate the crowds and show you the main highlights – notably Michelangelo’s Davidsaid to be anatomically perfect.

But Florence has more art venues than you think. Many of the city’s churches are worth visiting for their paintings. I’d also recommend a trip to some smaller art museums, especially the Bargello.

See eclectic sculptures in the Bargello Museum

Courtyard of the Bargello Museum, Florence

Courtyard of the Bargello Museum, Florence

Tucked away down a side street, this museum’s notched roofline seems to mimic the larger, showier Palazzo Vecchio nearby. A formidable-looking building, it was once the headquarters of Florence’s chief of police (bargello) under the Medicis, the political dynasty who ruled the Florentine Republic from the mid 1400s to 1737. The Bargello’s collections now mainly revolve around statues and sculptures transferred here from the Uffizi in the 19th century.

Stepping off the street into the Bargello’s open courtyard is a bit like entering a sanctuary: it’s instantly quieter. It’s unlikely you’ll need to wait in line to enter this museum. Inside, you can explore the collections at your own pace with an audio guide.

Pieces by Michelangelo are exhibited here, including Brutus. Made in 1538, it’s the only bust the artist ever created. It’s a great example of an artist responding to current affairs and the political climate of the time: Michelangelo is thought to be drawing a comparison between Julius Caesar’s notorious assassin and his patrons, the Medicis. Lorenzino de’ Medici had assassinated his cousin Alessandro de’ Medici (Florence’s then ruler) in 1537, claiming it was for the public good.

You’ll also discover Florence’s ‘other’ Davids, almost life-size bronze statues by Donatello, plus the earliest known portrait of Dante. You’ll find the piece that originally won Ghiberti the commission for the sculpted bronze doors of Florence’s Duomo’s baptistery. It’s a bronze relief depicting the biblical story of Abraham sacrificing Isaac, now sitting side by side with Brunelleschi’s rejected entry. Ghiberti’s version was judged to be more lyrical.

Explore the statues of Orsanmichele



This rectangular edifice of brick and stone is easy to pass by without understanding its significance. It’s a curious building that was erected on the site of the kitchen garden (orto) of the San Michele Monastery (which no longer exists). It was first used as a grain market, then a church. It’s difficult to tell its religious significance from the outside, but inside you’ll find a tabernacle with stained glass in jewel-like shades. There’s also a painting of the Madonna by Daddi that’s believed to have performed miracles, including saving worshippers from plague.

Most striking are the sculptures standing in the niches around the building (the originals are kept on Orsanmichele’s second floor). They each represent a patron saint of the city’s different arti (craft guilds). The guilds sought to outdo one another and commission more ambitious statues, from Ghiberti’s life-size John the Baptist for the cloth importers to Donatello’s poised St George for the arms makers. They’re a monument to the feverish commerce and one-upmanship in the 13th-century heyday of the arti.

What to do in Siena

View of Siena, Tuscany

View of Siena, Tuscany

One of Tuscany’s great cities, hilltop Siena is walled with yellow-brown brick buildings. Its meandering streets retain very much a medieval feel, converging on the fan-like space of the Piazza del Campo. This central public space hosts the city’s biannual daredevil horse race, Il Palio.

Siena had a contentious relationship with Florence. It constantly sought to outdo its richer rival, a sentiment that’s evident in the exuberantly decorated, Romanesque-Gothic façade of the Duomo (cathedral), festooned with expressive statues. The extravagance continues inside – but there’s so much going on here that it can all seem rather confusing at first glance; the full array and complexity of styles can go unnoticed.

Unlock the Duomo’s complex designs with a guide

Interior of Siena's cathedral

Interior of Siena's cathedral

The cathedral interior is crowded with pillars striped like black and white candy canes, and laid with marble mosaic floors. There are the frescoes of the Piccolini Library (left of the entrance) whose luminosity recall the illuminated books housed there. Pisano’s richly carved medieval wooden panels cradle the pulpit, while the Renaissance font is decorated with Donatello’s glided bronze plaques. Sumptuous, intricate designs are everywhere.

Look to the right-hand side of the Duomo, and you’ll see its huge, unfinished nave. It’s only one part of an extension halted by plague devastating the city in 1348. Guides can help convey what the finished project would have looked like, and explain the different elements of cathedral architecture in play, such as naves, side aisles and clerestories.

Admire a little-known view of Siena 

View of Siena from the Panorama del Facciatone

View of Siena from the Panorama del Facciatone

Many visitors to the Duomo climb its dome, but on a recent trip I discovered an even better 360-degree view over Siena: the terrace called the Panorama del Facciatone. To find it, head for the Museo dell’Opera del Duomo. This is the museum located in the side aisle of the never-completed nave, and it houses statues and other art from the cathedral. At the end of a gallery, a corkscrew flight of steps leads you to a terrace on the top of the unfinished nave.

From here, you look out not only over the Piazza del Campo and the entire city , but across to the cathedral’s dome and its striped bell tower. They punctuate the city skyline along with the soaring bell tower of Siena’s town hall.

Our expert tips for visiting the Leaning Tower of Pisa

Lose yourself in Lucca

Piazza in Lucca

Piazza in Lucca

A 30 minute journey north of Pisa by car brings you to the town of Lucca, rising out of a plateau. It’s encircled by intact ramparts originally built by the Romans in 2 BC; you’re still able to walk on them today.

A guide is useful for helping you get your bearings, but I think Lucca is best experienced by just wandering around, following your whims. It’s a compact maze of Gothic palazzos and cobbled, medieval-era alleyways opening out unexpectedly into piazzas. The most striking one, the Piazza dell’Anfiteatro, is a circular shape, built on the remains of a Roman auditorium. You’ll stumble constantly upon churches or small squares full of locals enjoying aperitivi (pre-dinner drinks).

One church, San Michele in Foro, particularly intrigued me for one novelty inside. A statue of the Archangel Michael crowns the top of a tall Romanesque façade, and my guide pointed out some steps leading up to it. They were used to operate the mechanism that made Michael’s wings ‘flap’.

In addition to being a destination in its own right, Lucca is a good place to stay when you’re exploring the area. It’s a little over an hour drive to various points of interest around the region: the villages of the Cinque Terre, the Garfagnana Valley and the Grotta del Vento (Cave of the Wind), or the city of Pontremoli.

Ancient stelae and Baroque palaces in Pontremoli

San Gimignano

San Gimignano

Ringed by a wall, the small hill top town of San Gimignano announces its presence through a number of brick and stone towers rising above a patchwork of fields, olive groves and vineyards. It’s a view that has barely altered since the 12th century, when pilgrims would stop off there en route to Rome. At that time, the towers were status symbols, signifying a family’s wealth. They also served a security purpose, acting as a sort of medieval panic room if the town ever came under attack.

Today, San Gimignano is a well-preserved enclave to amble around for an afternoon: you’ll come across piazzas with crumbling stone wells, gourmet food shops, and gelaterías. Most visitors ascend the 218 steps of the one tower open to the public, the Torre Grossa. My advice is to bypass this long, hot hike and walk behind the town’s Duomo up to the area known as the Rocca de Montestaffoli.

Here, you enter a quiet green space with a scattering of flower beds. You’re up on a raised ridge, in the skeleton of a fortress that once belonged to a bishop. If you climb the 30 or so steps of one of the fort’s ruined towers, you’ll get what for me is the best view over San Gimignano: walls draped in banks of wisteria and the Torre Grossa in the foreground, with the vine-covered hillsides of the surrounding countryside beyond. 

Food experiences in Tuscany

Try honey tasting at Castello di Meleto

Honey tasting at Castello di Meleto

Honey tasting at Castello di Meleto

Wine is a well-known exponent of Tuscany’s Chianti region, which falls mainly between Florence and Siena, but honey making is another artisan tradition stretching back centuries.

You can visit Castello di Meleto, an 11th-century quadrangle of a castle and its wine estate, for excellent wine tasting, but a less conventional experience is exploring the honeys produced on site.

The castle sits amid a classic Tuscan landscape of low-lying hills, olive groves, and corridors of cypress trees. Dressed in full beekeeping attire, one of the Castello’s honey farmers will lead you down to the hives. After calming the bees with a smoker, you’ll take out different frames and try and identify the queen. Back at the castle, you’ll be presented with different varieties of honey served in wine glasses.  

During the tasting, you’ll sample all kinds of locally grown honey. Honey from chestnut trees can be more bitter than other varieties, while others have a floral taste. The castello’s honey specialists can advise which variety is best eaten on toast, or even used in barbecue sauces. You’ll also try local honey spread on slices of cheese, a regional specialty.

Go truffle hunting and enjoy a gourmet lunch

Truffle hunting near Palaia

Truffle hunting near Palaia

An hour’s car ride from Florence, the deciduous woodland near the village of Palaia offers particularly rich pickings. Some of the region’s best black truffles grow here, under a mass of bracken, foliage and tangled undergrowth. In Italy, you can hunt for truffles anywhere as long as it doesn’t involve passing through a gate into private property.

You can go for walks in these woods with a local truffle expert, Lucca, and his dog, Bilba. She’s been specially trained to sniff out truffles in the earth.

On my visit, I was unsure at first whether we’d strike lucky. But a little way into the trees, Bilba started running in circles. Suddenly, she began to dig. Lucca pulled her away just in time before her claws damaged the gnarly black truffle she was unearthing. He explained that pigs were once used to hunt out truffles, but they inevitably ate them, so dogs had taken their place.

I eventually came back with five black truffles – not a bad haul. However, the rare white truffles – the real gold dust – remained elusive on this occasion.

After your truffle hunt, you’ll return to the village to explore the Savini family’s showroom, located on the same site as their small-scale factory. Here, they make all kinds of delicacies, fine foods and condiments using truffles, including truffle oils, honeys, pestos and salts. As soon as you enter the buildings, the pungent, wet-earth scent of truffles rushes into your nose.

The Savini have been harvesting truffles in this area since the 1920s. In their showroom, you can see photographs and press clippings documenting how their business has grown over the years, as well as a photo of the most expensive truffle ever found.

Lunch, as you might expect, is entirely truffle-themed. It’s held in a dining room just off the showroom. Truffles are shaved into or used in every course, from an antipasti of truffle-cured salami to delicate nut and truffle ice-cream served for dessert.

Best places to stay in Tuscany

Monteverdi, Castiglioncello del Trinoro


Villa Il Poggiale, San Casciano in Val di Pesa

Villa Il Poggiale

Florence makes a great base for exploring Tuscany, but it’s also possible to stay in the countryside. My pick would be Monteverdi, a property that’s part of a minute hilltop hamlet. It was converted into a hotel by an American lawyer after the village fell into decline following World War II. The rooms and villas are dispersed among the village and feature elegant, modern decor. Your room may be situated next door to the home of a retired local couple, or across the street from the hotel restaurant.

I also like Villa Il Poggiale. This warren-like hotel, formerly the home of a Tuscan nobleman, has great views across the surrounding vineyards.

Offering more flexibility and variety than staying at a vineyard, Siena also makes a convenient base for exploring Tuscany’s wine country. From there, you can dip in and out of different vineyards across the nearby Chianti and Brunello di Montalcino regions and still have the option of returning to the city’s many restaurants in the evening. It’s also only an hour’s drive from San Gimignano.  

In the city, I’m particularly fond of staying at the Grand Hotel Continental, set in a converted 17th-century palazzo. The high ceilings and large windows give it an airy charm and it’s located just steps from the central Piazza del Campo. 

Best time to visit Tuscany

The region is at its loveliest, weather-wise, in late spring (May) and during September and October. The summer months of July and August can be uncomfortably hot. I’d avoid August as many Italians go to the coast during this time, and some businesses shut down completely.

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Start thinking about your experience. These itineraries are simply suggestions for how you could enjoy some of the same experiences as our specialists. They’re just for inspiration, because your trip will be created around your particular tastes.

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